Novel phenylpropanoid–amino acid adducts from Ligusticum chuanxiong†,Organic Chemistry Frontiers

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Novel phenylpropanoid–amino acid adducts from Ligusticum chuanxiong†
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2018-03-06 00:00:00 , DOI: 10.1039/c8qo00012c
Xu Zhang _{1,

2,

3,

4,

5} , Bing Han _{1,

2,

3,

4,

5} , Zi-Ming Feng _{1,

2,

3,

4,

5} , Ya-Nan Yang _{1,

2,

3,

4,

5} , Jian-Shuang Jiang _{1,

2,

3,

4,

5} , Pei-Cheng Zhang _{1,

2,

3,

4,

5}

Affiliation

Eight new amino acid derivatives (1–8) and two known compounds (9–10) were isolated from the rhizome of Ligusticum chuanxiong Hort. Their structures were established using UV, IR, HRESIMS, and NMR data. Notably, phenylpropanoid–amino acid adducts 1–6 are the first reported natural products, which possess a unique adduct structure. In addition, their analogues (1–5) were successfully synthesized by nucleophilic substitution and hydrolysis. The absolute configurations of 1–5 were determined by comparison of the specific rotations with those of their analogues and the natural amino acid methyl ester hydrochloride in acetic acid. In addition, these compounds were all evaluated for their neuroprotective effects, and compound 9 showed a moderate protective effect towards human neuroblastoma SH-SY5Y cell injury induced by H₂O₂.

中文翻译：

新颖苯丙氨基从加成物川芎†

从川gust （Ligusticum chuanxiong Hort ）的根茎中分离出八个新的氨基酸衍生物（1–8）和两个已知的化合物（9–10）。使用UV，IR，HRESIMS和NMR数据确定其结构。值得注意的是，苯丙烷-氨基酸加合物1-6是最早报道的天然产物，具有独特的加合物结构。此外，它们的类似物（1-5）是通过亲核取代和水解成功合成的。1-5的绝对配置通过将比旋光度与其类似物的旋光度和乙酸中的天然氨基酸甲酯盐酸盐的旋光度进行比较来确定。另外，评估了这些化合物的神经保护作用，化合物9显示出对由H ₂ O ₂诱导的人神经母细胞瘤SH-SY5Y细胞损伤的中等保护作用。

更新日期：2018-03-06

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